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Winter Park Homes For Sale & Real Estate - 285 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 2835 ROUEN AVENUE, WINTER PARK, FL 32789

    $400,000Listed 10/29/2020 9:27PM   MLS ID: O5902069

    For Sale O5902069 - 2835 ROUEN AVENUE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1914
       Built: 1959   Tax: $3,590 (2019)
    Community: Winter Park Manor
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,491 (change assumption)
    Mortgage ($2,192) + Taxes in 2019 ($299)

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    Taxes:$3,590

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle


  • 2356 COLDSTREAM DRIVE, WINTER PARK, FL 32792

    $478,90042 Days on yellowkey   MLS ID: O5893560

    23 Days Off yellowkey (back on 10/21/2020)

    REDUCED by $1,000 (0.2%) on 10/29/2020

    For Sale O5893560 - 2356 COLDSTREAM DRIVE, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1619
       Built: 1959   Tax: $4,573 (2019)
    Community: Brookshire Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,624) + Taxes in 2019 ($381)

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    Taxes:$4,573

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 4953 ARDMORE DRIVE, WINTER PARK, FL 32792

    $289,900Listed 10/29/2020 7:36PM   MLS ID: O5902478

    For Sale O5902478 - 4953 ARDMORE DRIVE, WINTER PARK, FL 32792 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1443
       Built: 1979   Tax: $2,228 (2019)
    Community: Wrenwood Unit 3 2Nd Add
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $1,774 (change assumption)
    Mortgage ($1,588) + Taxes in 2019 ($186)

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    Taxes:$2,228

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 176 BALFOUR DRIVE UNIT 4, WINTER PARK, FL 32792

    $240,000193 Days on yellowkey   MLS ID: O5858199

    4 Days Off yellowkey (back on 10/29/2020)

    REDUCED by $20,000 (7.7%) on 10/13/2020

    For Sale O5858199 - 176 BALFOUR DRIVE UNIT 4, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1740
       Built: 1980
    Monthly Fee: $400
       Tax: $1,258 (2019)
    Community: Winter Park Pointe 01
    Pool: No

    Condo


    Estimated Monthly Payment: $1,820 (change assumption)
    Mortgage ($1,315) + Fees ($400) + Taxes in 2019 ($105)

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    Taxes:$1,258

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 332 HARRIS AVENUE, WINTER PARK, FL 32789

    $399,000Listed 10/29/2020 3:43PM   MLS ID: O5901828

    For Sale O5901828 - 332 HARRIS AVENUE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,266 (2019)
    Community: Sylvan Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,458 (change assumption)
    Mortgage ($2,186) + Taxes in 2019 ($272)

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    Taxes:$3,266

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 2647 CAYMAN WAY, WINTER PARK, FL 32792

    $190,000Listed 10/29/2020 3:42PM   MLS ID: O5902546

    For Sale O5902546 - 2647 CAYMAN WAY, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1467
       Built: 1978
    Monthly Fee: $78
       Tax: $2,005 (2019)
    Community: Windward Square Sec 2
    Pool: No

    Townhouse


    Estimated Monthly Payment: $1,286 (change assumption)
    Mortgage ($1,041) + Fees ($78) + Taxes in 2019 ($167)

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    Taxes:$2,005

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 603 WARRENTON ROAD, WINTER PARK, FL 32792

    $199,900Listed 10/29/2020 12:00PM   MLS ID: O5902484

    For Sale O5902484 - 603 WARRENTON ROAD, WINTER PARK, FL 32792 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1233
       Built: 1984
    Monthly Fee: $75
       Tax: $2,758 (2019)
    Community: Winter Park Pines Patio Homes
    Pool: No

    Villa


    Estimated Monthly Payment: $1,400 (change assumption)
    Mortgage ($1,095) + Fees ($75) + Taxes in 2019 ($230)

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    Taxes:$2,758

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 2594 FORFARSHIRE DRIVE, WINTER PARK, FL 32792

    $425,000Listed 10/29/2020 12:00PM   MLS ID: O5901814

    For Sale O5901814 - 2594 FORFARSHIRE DRIVE, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1944
       Built: 1962   Tax: $3,258 (2020)
    Community: Brookshire Heights 2Nd Add
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,600 (change assumption)
    Mortgage ($2,329) + Taxes in 2020 ($272)

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    Taxes:$3,258

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 1500 HARRIS CIRCLE, WINTER PARK, FL 32789

    $749,90066 Days on yellowkey   MLS ID: O5887666

    44 Days Off yellowkey (back on 10/29/2020)

    For Sale O5887666 - 1500 HARRIS CIRCLE, WINTER PARK, FL 32789 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1915
       Built: 1994   Tax: $5,173 (2020)
    Community: Sylvan Lake Shores
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,540 (change assumption)
    Mortgage ($4,109) + Taxes in 2020 ($431)

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    Taxes:$5,173

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 999 ARAGON AVENUE, WINTER PARK, FL 32789

    $409,9001 Day on yellowkey   MLS ID: O5902327

    For Sale O5902327 - 999 ARAGON AVENUE, WINTER PARK, FL 32789 45 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1777
       Built: 2003   Tax: $4,444 (2019)
    Community: Seville Park
    Pool: No

    1/2 Duplex


    Estimated Monthly Payment: $2,616 (change assumption)
    Mortgage ($2,246) + Taxes in 2019 ($370)

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    Taxes:$4,444

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 3462 BOWMAN DRIVE, WINTER PARK, FL 32792

    $325,0001 Day on yellowkey   MLS ID: O5900833

    For Sale O5900833 - 3462 BOWMAN DRIVE, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2158
       Built: 1968   Tax: $2,096 (2019)
    Community: Eastbrook Sub Unit 12
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,955 (change assumption)
    Mortgage ($1,781) + Taxes in 2019 ($175)

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    Taxes:$2,096

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 1913 WOODCREST DRIVE UNIT B, WINTER PARK, FL 32792

    $214,5001 Day on yellowkey   MLS ID: O5902297

    For Sale O5902297 - 1913 WOODCREST DRIVE UNIT B, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 987
       Built: 1973
    Monthly Fee: $325
       Tax: $752 (2019)
    Community: Oaks Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $1,563 (change assumption)
    Mortgage ($1,175) + Fees ($325) + Taxes in 2019 ($63)

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    Taxes:$752

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 1750 EDWIN BOULEVARD, WINTER PARK, FL 32789

    $1,495,0001 Day on yellowkey   MLS ID: O5902080

    For Sale O5902080 - 1750 EDWIN BOULEVARD, WINTER PARK, FL 32789 49 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 4108
       Built: 2020   Tax: $5,702 (2019)
    Community: Campo Bello
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $8,667 (change assumption)
    Mortgage ($8,192) + Taxes in 2019 ($475)

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    Taxes:$5,702

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle


  • 820 N LAKEMONT AVENUE, WINTER PARK, FL 32792

    $890,0001 Day on yellowkey   MLS ID: O5902124

    For Sale O5902124 - 820 N LAKEMONT AVENUE, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3113
       Built: 2018   Tax: $10,481 (2019)
    Community: Acreage
    Pool: No

    Single Family


    Estimated Monthly Payment: $5,750 (change assumption)
    Mortgage ($4,877) + Taxes in 2019 ($873)

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    Taxes:$10,481

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle


  • 1830 GIPSON GREEN Lane, WINTER PARK, FL 32789

    $4,195,0001 Day on yellowkey   MLS ID: O5902307

    For Sale O5902307 - 1830 GIPSON GREEN Lane, WINTER PARK, FL 32789 50 photos

    Bed: 5   Bath: 6.0
    Liv Area Sq Ft: 6444
       Built: 1999   Tax: $40,491 (2020)
    Community: Boiley Green Sub
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $26,360 (change assumption)
    Mortgage ($22,986) + Taxes in 2020 ($3,374)

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    Taxes:$40,491

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 1113 VIA DEL MAR, WINTER PARK, FL 32789

    $759,0001 Day on yellowkey   MLS ID: O5901816

    For Sale O5901816 - 1113 VIA DEL MAR, WINTER PARK, FL 32789 7 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1770
       Built: 1957   Tax: $2,904 (2020)
    Community: Tuscany Terrace
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,401 (change assumption)
    Mortgage ($4,159) + Taxes in 2020 ($242)

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    Taxes:$2,904

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 2804 SCARLET ROAD, WINTER PARK, FL 32792

    $349,90055 Days on yellowkey   MLS ID: V4915354

    REDUCED by $19,100 (5.2%) on 10/29/2020

    For Sale V4915354 - 2804 SCARLET ROAD, WINTER PARK, FL 32792 15 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1838
       Built: 1962   Tax: $3,976 (2019)
    Community: Winter Park Pines
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,249 (change assumption)
    Mortgage ($1,917) + Taxes in 2019 ($331)

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    Taxes:$3,976

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 200 SAINT ANDREWS BOULEVARD UNIT 906, WINTER PARK, FL 32792

    $145,0001 Day on yellowkey   MLS ID: O5902206

    For Sale O5902206 - 200 SAINT ANDREWS BOULEVARD UNIT 906, WINTER PARK, FL 32792 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 727
       Built: 1970   Tax: $1,226 (2019)
    Community: Four Seasons Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $897 (change assumption)
    Mortgage ($795) + Taxes in 2019 ($102)

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    Taxes:$1,226

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 1871 OGLESBY AVENUE, WINTER PARK, FL 32789

    $225,00038 Days on yellowkey   MLS ID: O5894246

    REDUCED by $24,000 (9.6%) on 10/28/2020

    For Sale O5894246 - 1871 OGLESBY AVENUE, WINTER PARK, FL 32789 30 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1132
       Built: 1951   Tax: $659 (2019)
    Community: Olympia Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,288 (change assumption)
    Mortgage ($1,233) + Taxes in 2019 ($55)

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    Taxes:$659

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2019

    Middle School: College Park Middle


  • 7732 WAUNATTA COURT, WINTER PARK, FL 32792

    $1,268,0001 Day on yellowkey   MLS ID: O5900681

    For Sale O5900681 - 7732 WAUNATTA COURT, WINTER PARK, FL 32792 68 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3417
       Built: 2015
    Monthly Fee: $6
       Tax: $13,373 (2019)
    Community: Lake Waunatta
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $8,068 (change assumption)
    Mortgage ($6,948) + Fees ($6) + Taxes in 2019 ($1,114)

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    Taxes:$13,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Park listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, South Broward Board of REALTORS®, MIAMI MLS, JTHS MLS, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2020 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.